Diisopropylethylamine → 2-(Cyclopropylsulfonyl)-3-{[4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidin-1-yl]carbonyl}-6-(trifluoromethyl)pyridine

HRID 1873841Notes

Reaction equation

HRID 1873841 reaction equation
[CH3:1][C:2]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)(=[O:6])=[O:5])[CH3:3].[CH:23]1([S:26]([C:29]2[N:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][C:30]=2[C:31](O)=[O:32])(=[O:28])=[O:27])[CH2:25][CH2:24]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>[NH4+].[Cl-].CN(C)C=O>[CH:23]1([S:26]([C:29]2[C:30]([C:31]([N:20]3[CH2:21][CH2:22][CH:17]([C:2]([CH3:1])([S:4]([C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=4)(=[O:5])=[O:6])[CH3:3])[CH2:18][CH2:19]3)=[O:32])=[CH:34][CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[N:37]=2)(=[O:27])=[O:28])[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 594474094-(1-Methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidineHCID 684877982-(Cyclopropylsulfonyl)-6-(trifluoromethyl)nicotinic acid

Product 1

HCID 252557852-(Cyclopropylsulfonyl)-3-{[4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidin-1-yl]carbonyl}-6-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a 50 ml round bottom flask was added 4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine (1.64 g, 4.88 mmol), 2-(cyclopropylsulfonyl)-6-(trifluoromethyl)nicotinic acid (1.2 g, 4.06 mmol), Bop reagent (2.16 g, 4.88 mmol), diisopropylethyl amine (1.42 ml, 8.13 mmol) and 10 ml dimethylformamide. The resulting solution was stirred at room temperature 10 minutes. It was diluted with 60 ml NH4Cl solution and extracted with 60 ml ethyl acetate. The organics were dried over sodium sulfate, filtered and concentrated. The sesidue was purified on silica gel column eluted with 2:1 ethyl acetate/hexane. The desired fraction was collected and concentrated. The residue was further purified on prep-TLC to give title compound as a white solid.

Workup

  1. extractionextracted with 60 ml ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe sesidue was purified on silica gel column
  6. washeluted with 2:1 ethyl acetate/hexane
  7. customThe desired fraction was collected
  8. concentrationconcentrated
  9. customThe residue was further purified on prep-TLC

Sources & evidence

ORD record
ord-f51855d3f41243778c9704316ca560cd
Source dataset
uspto-grants-2012_11
Patent number
US08304434B2

Reaction notes

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